Global Patent Index - EP 0619307 A1

EP 0619307 A1 19941012 - Process for the preparation of 2-halogeno-pyridine derivatives.

Title (en)

Process for the preparation of 2-halogeno-pyridine derivatives.

Title (de)

Verfahren zur Herstellung von 2-Halogen-pyridin-derivaten.

Title (fr)

Procédé pour la préparation de dérivés de 2-halogéno-pyridine.

Publication

EP 0619307 A1 19941012 (DE)

Application

EP 94104674 A 19940324

Priority

DE 4311247 A 19930406

Abstract (en)

The present invention relates to a process for the preparation of 2-halogenopyridine derivatives of the general formula (I) <IMAGE> in which X represents halogen and Y represents halogeno, nitro, formyl, cyano, carboxyl, carbamoyl, alkyl, halogenoalkyl, alkoxyalkyl, dialkoxyalkyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, with the exception of compounds in which X represents chlorine and Y simultaneously methyl, which is characterised in that, in a first step, pyridine 1-oxides of the general formula (II) <IMAGE> in which Y has the abovementioned meaning are reacted with an organic nitrogen base A and an electrophilic compound, if appropriate in the presence of a diluent, to give compounds of the general formula (III) <IMAGE> in which A represents the radical of an organic nitrogen base, Y has the abovementioned meaning and Z<-> represents an anion formed from an electrophilic compound, if appropriate the compounds of the formula (III) are isolated as crude products or if appropriate further purified, and, in a second step, these compounds are reacted with a halogenating agent at temperatures between 10@C and 150@C, if appropriate in the presence of an alkyl halide and if appropriate in the presence of a diluent. The invention furthermore relates to the new compounds of the formula (III).

Abstract (de)

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von 2-Halogen-pyridin-derivaten der allgemeinen Formel (I) <IMAGE> in welcher X: für Halogen steht und; Y: für Halogen, Nitro, Formyl, Cyano, Carboxy, Carbamoyl, Alkyl, Halogenalkyl, Alkoxyalkyl, Dialkoxyalkyl, Alkoxycarbonyl, Alkylaminocarbonyl oder Dialkylaminocarbonyl steht, ausgenommen Verbindungen, in denen X für Chlor und Y gleichzeitig für Methyl steht, das dadurch gekennzeichnet ist, daß man in einer ersten Stufe Pyridin-1-oxide der allgemeinen Formel (II) <IMAGE> in welcher Y: die oben angegebene Bedeutung hat, mit einer organischen Stickstoffbase A und einer elektrophilen Verbindung, gegebenenfalls in Gegenwart eines Verdünnungsmittels, zu Verbindungen der allgemeinen Formel (III) umsetzt <IMAGE> in welcher A: für den Rest einer organischen Stickstoffbase steht, Y: die oben angegebene Bedeutung hat und; Z<->: für ein aus einer elektrophilen Verbindung gebildetes Anion steht, die Verbindungen der Formel (III) gegebenenfalls als Rohprodukte isoliert oder gegebenenfalls weiter reinigt und in einer zweiten Stufe mit einem Halogenierungsmittel, gegebenenfalls in Gegenwart eines Alkylhalogenids und gegebenenfalls in Gegenwart eines Verdünnungsmittels bei Temperaturen zwischen 10°C und 150°C umsetzt. Ferner betrifft die Erfindung die neuen Verbindungen der Formel (III).

IPC 1-7

C07D 213/61; C07D 213/85

IPC 8 full level

C07D 213/61 (2006.01); C07D 213/74 (2006.01); C07D 213/78 (2006.01); C07D 213/85 (2006.01)

CPC (source: EP)

C07D 213/61 (2013.01); C07D 213/74 (2013.01); C07D 213/85 (2013.01)

Citation (search report)

  • [XP] EP 0556683 A1 19930825 - BAYER AG [DE] & DE 4204920 A
  • [XD] EP 0463464 A1 19920102 - BAYER AG [DE]
  • [XD] EP 0439745 A2 19910807 - BAYER AG [DE]
  • [XD] EP 0438691 A1 19910731 - BAYER AG [DE]
  • [X] CHEMICAL ABSTRACTS, vol. 89, no. 25, 18 December 1978, Columbus, Ohio, US; abstract no. 215188r, A.R. KATRITZKY ET AL.: "Preparation of some novel pyridone derivatives." page 574; & PAKISTAN JOURNAL OF SCIENCE AND INDUSTRIAL RESEARCH, vol. 21, no. 1, 1978, KARACHI, PAKISTAN, pages 1 - 4
  • [X] A.R. KATRITZKY ET AL.: "Nucleophilic displacement of N-aryl and heteroaryl groups. Part 5. Conversion of 2-aminopyridines into 2-pyridones.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 11, 1983, LETCHWORTH GB, pages 2623 - 2627
  • [X] A.S. AFRIDI ET AL.: "Synthesis, spectroscopic properties, and chemistry of 4,6-diphenyl-2-pyridones and 4,6-diphenylpyridine-2-thiones and their relationship to isomeric species.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 12, 1977, LETCHWORTH GB, pages 1436 - 1445
  • [X] CHEMICAL ABSTRACTS, vol. 112, no. 3, 15 January 1990, Columbus, Ohio, US; abstract no. 20851n, R.H. BRADBURY ET AL.: "Cephalosporin derivatives." page 489; & AU 584898 A
  • [X] CHEMICAL ABSTRACTS, vol. 107, no. 22, 30 November 1987, Columbus, Ohio, US; abstract no. 211056p, G. GUIFA ET AL.: "Synthesis of the new color reagent 1-(5'-bromo-2-pyridyl)-5-(4'-nitrophenyl-3-(2'-furyl)formazan and its color reaction with zinc." page 877; & GAODENG XUEXIAO HUAXUE XUEBAO, vol. 8, no. 5, 1987, CHANGCHUN CHINA, pages 421 - 423
  • [X] CHEMICAL ABSTRACTS, vol. 87, no. 6, 8 August 1977, Columbus, Ohio, US; abstract no. 41587m, R. ZALEWSKI ET AL.: "Studies on the quantitative determination of pyridine bases in coal tars. II. Reactions of chloro-2,4-dinitrobenzene and 2-chloro-5-nitropyridine with methyl pyridines." page 127; & CHEMICAL ANALYSIS, vol. 21, no. 6, 1976, WARSAW, pages 1275 - 1281
  • [X] CHEMICAL ABSTRACTS, vol. 85, no. 6, 9 August 1976, Columbus, Ohio, US; abstract no. 40429h, R. ZALEWSKI ET AL.: "Studies on the quantitative determination of pyridine in coal tars. I. The alkaline hydrolysis of the products of the reactions of some chloronitro compounds with pyridine." page 538; & CHEMICAL ANALYSIS, vol. 21, no. 1, 1976, WARSAW, pages 73 - 83
  • [X] N. DENNIS ET AL.: "Dimer of 1-(5-nitro-2-pyridyl)-3-oxidopyridinium and its reactions.", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 13, 1974, LETCHWORTH GB, pages 500 - 501
  • [X] G.B. BARLIN ET AL.: "Kinetics of reactions in heterocycles. VIII. Preparations and reactivity of trimethylammonio derivatives of aza monocycles (pyridine and pyrimidine) towards hydroxide ion.", JOURNAL OF THE CHEMICAL SOCIETY, SECTION B: PHYSICAL ORGANIC CHEMISTRY, no. 8, 1981, LETCHWORTH GB, pages 1675 - 1682

Designated contracting state (EPC)

BE CH DE DK ES FR GB IT LI NL

DOCDB simple family (publication)

DE 4311247 A1 19941013; BR 9401396 A 19941018; CN 1101036 A 19950405; EP 0619307 A1 19941012; HU 9400973 D0 19940628; HU T67563 A 19950428; JP H06306049 A 19941101

DOCDB simple family (application)

DE 4311247 A 19930406; BR 9401396 A 19940405; CN 94103496 A 19940406; EP 94104674 A 19940324; HU 9400973 A 19940406; JP 8373794 A 19940331